Seitetsu Kagaku Co., Ltd.

Masao Kawamura

Kunioki Kato

Tadaaki Nishi

Hiroshi Goda

Makoto Sato

Akira Onoe

Yasuto Okubo

Taiko Seno

Hirosuke Fukuda

Seiichi Akutsu

Tsuyoshi Morishita

Hiroshi Mizokami

Kazuhiro Hamatani

Tadashi Kanazawa

Syuzi Takagi

Masato Yoshikawa

Kiyoshi Sawada

Tomiharu Amitani

Michio Suzuki

Kenzo Kobayashi

Hiro Tsuchiya

Hirokazu Kagano

Masahide Takahashi

Kazuyuki Nakayama

Masakazu Hatta

Akio Nakatsuka

Nobuyuki Kitagishi

Nobuhiro Koune

In a process of producing high purity bis(4-hydroxyphenyl)sulfides which comprises reacting phenols with sulfur dichloride in an organic solvent, the improvement comprising: reacting the phenols with sulfur dichloride in a nonpolar organic solvent; removing partly or wholly the nonpolar organic solvent after the reaction; adding a polar organic solvent to the reaction mixture to dissolve the reaction mixture therein at elevated temperatures; and crystallizing out the high purity bis(4-hydroxyphenyl)sulfides. There is further provided a high performance heat-sensitive recording material which comprises high purity bis(4-hydroxy-3-methylphenyl)sulfide thus prepared and having a melting point in the range of from 123.9.degree. C. to 124.9.degree. C. as a developer and a fluoran compound as a color former.

Process of producing high purity bis(4-hydroxyphenyl)sulfides and

In a process of producing high purity bis(4-hydroxyphenyl) sulfides which comprises reacting phenols with sulfur dichloride in organic solvents, the improvement comprising: reacting the phenols with sulfur dichloride in nonpolar organic solvents; removing partly or wholly the nonpolar organic solvents after the reaction; adding polar organic solvents to the reaction mixture to dissolve the reaction mixture therein at elevated temperatures; and crystallizing out the high purity bis(4-hydroxyphenyl)sulfides. There is further provided a high performance heat-sensitive recording material which comprises high purity bis(4-hydroxy-3-methylphenyl)sulfide thus prepared and having a melting point in the range of from 123.9.degree. C. to 124.9.degree. C. as a developer and a fluoran compound as a color former.

Heat-sensitive recording materials containing high purity

Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are susceptible to electrophilic substitution reactions, and the acetylation, nitration, sulfonation and halogenation of the compounds provide 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-nitro-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acid and 5-halo-2-(.alpha.-alkoxyimino)ethylthiophenes, respectively. The hydrolysis of 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes readily provides a known compound, 2,5-diacetylthiophene which is an important intermediate for the production of medicines, whereas the haloform reaction provides novel compounds, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenecarboxylic acids, the hydrolysis of which compounds readily provides a known compound, 5-acetyl-2-thiophenecarboxylic acids, an important intermediate for the production of medicines. The hydrolysis of 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acids and their salts provide novel 5-acetyl-2-thiophenesulfonic acid and its salts, respectively. Novel compounds, 2-(.alpha.-alkoxyimino)ethylithiophenes are obtained either by 0-alkylation of 2-acetylthiophene oxime or by directly reacting 2-acetylthiophene with an 0-alkylhydroxylamine.

Novel thiophene derivatives and methods for producing the same

Process for preparing 2-alkyl-5-haloacetylbenzenesulfonamide represented by the general formula (1), ##STR1## (wherein R.sup.1 is an alkyl group having 1 to 5 carbon atoms; and X is a chlorine atom, bromine atom or iodine atom), characterized by halogenating a 5-acetyl-2-alkylbenzenesulfonamide represented by the general formula (2), ##STR2## (wherein R.sup.1 is the same as defined above) in a lower alcohol represented by the general formula (3),

Salt of 5-acetyl-2-alkylbenzenesulfonic acid

Process for preparing N,N-dialkylaniline salt of 5-acetyl-2-alkylbenzene

A method of producing alkali metal benzenesulfinates having the general formula of ##STR1## wherein M represents Na or K, which comprises: reacting nitrophenylphenyl sulfones having the general formula of ##STR2## wherein n is an integer of 1 or 2, with alkali metal thiophenolates having the general formula of ##STR3## in solvents. The reaction produces also nitrophenylphenyl sulfides as by-products in equimolar amounts to the alkali metal benzenesulfinates, and the oxidation of the sulfides provides the starting nitrophenylphenyl sulfones. A method of producing the nitrophenylphenyl sulfones is also provided wherein the sulfides are oxidized with hydrogen peroxide in the presence both of water-soluble tungstates or molybdates and of phase transfer catalysts in a two-phase heterogeneous solvent.

Method of producing alkali metal benzenesulfinates

Novel compounds, 4-tert.-butyl-1,2-benzenedithiol and bis(4-tert.-butyl-1,2-dithiophenolate) metal complexes having the general formula of ##STR1## wherein M represents a trivalent transition metal, and A represents a quarternary ammonium are provided. The novel benzenedithiol is produced by reacting 4-tert.-butylbenzenethiol or di(4-tert.-butylphenyl)disulfide with sulfur monochloride in the presence of iodine or a Lewis acid in a solvent, and then reducing the resultant product with a metal selected from the group consisting of zinc, tin, iron and aluminum in the presence of an acid. The novel Cu, Co and Ni complexes are produced by reacting the benzenedithiol with a salt of the corresponding divalent transition metal in the presence of an alkoxide metal or a hydride metal and a quarternary ammonium salt in a solvent under an oxidative atmosphere. The complexes strongly absorb rays in the region of ultraviolet, visible or near infrared, and are useful intermediates for the production of optical information recording media.

4-tert.-butyl-1,2-benzenedithiol, complex compounds derived therefrom,

Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are susceptible to electrophilic substitution reactions, and the acetylation, nitration, sulfonation and halogenation of the compounds provide 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-nitro-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acid and 5-halo-2-(.alpha.-alkoxyimino)ethylthiophenes, respectively. The hydrolysis of 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes readily provides a known compound, 2,5-diacetylthiophene which is an important intermediate for the production of medicines, whereas the haloform reaction provides novel compounds, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenecarboxylic acids, the hydrolysis of which compounds readily provides a known compound, 5-acetyl-2-thiophenecarboxylic acids, an important intermediate for the production of medicines. The hydrolysis of 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acids and their salts provide novel 5-acetyl-2-thiophenesulfonic acid and its salts, respectively. Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are obtained either by 0-alkylation of 2-acetylthiophene oxime or by directly reacting 2-acetylthiophene with an 0-alkylhydroxylamine.

Thiophene derivatives and methods for producing the same

A process for producing polythiobisphenols which comprises: reacting a phenol having the general formula ##STR1## wherein each R independently represents a hydrogen, a halogen or an alkyl, with sulfur monochloride in a polar organic solvent in the presence of a nitrogen-containing organic compound as a catalyst which is selected from the group consisting of tertiary amines, quaternary ammoniums, alkylated acid amides and heteroaromatic compounds, in amounts of about 1-30% by weight based on the amount of the phenol used. As a catalyst, bromine or an alkali metal halide is also usable. A novel process for producing mercaptophenols by the hydrogenolysis of polythiobisphenols in the presence of a nickel catalyst is also disclosed. Raney nickel catalyst which is in advance poisoned with an organosulfur compound in which the sulfur atom has unshared electron pairs is especially effective as a catalyst.

Process for producing polythiobisphenols and process for producing

An anti-I sorbent which comprises as I blood group substances at least two materials selected from the group consisting of mucin and milk derived from Eutheria and ovomucoid from Ornithurae. The use of the anti-I sorbent inhibits the formation of false positive agglutination caused by anti-I autoantibody.

Anti-I sorbent

A process for preparing uridine diphosphate-N-acetylgalactosamine, which comprises treating a reaction solution obtained by the enzymatic conversion of uridine diphosphate-N-acetylglucosamine to uridine diphosphate-N-acetylgalactosamine, with uridine diphosphate-N-acetylglucosamine pyrophosphorylase to decompose the remaining uridine diphosphate-N-acetylglucosamine in the solution and then separating therefrom the uridine diphosphate-N-acetylgalactosamine for purification. In one aspect of this invention, it relates to a method for measuring the activity of .alpha.-N-acetylgalactosaminyl transferase characterized by the use of said reaction solution as the substrate for the transferase.

Process for preparing uridine diphosphate-N-acetylgalactosamine

A process for producing p-hydroxybenzaldehyde through p-aminobenzaldehyde from p-nitrotoluene, comprising reacting p-nitrotoluene with sodium polysulphide in an alcohol-alkali aqueous solution mixed solvent in the presence or absence of an aprotic polar compound to produce p-aminobenzaldehyde, diazotizing the p-aminobenzaldehyde and then hydrolyzing the diazotized p-aminobenzaldehyde to produce p-hydroxybenzaldehyde.

Process for producing p-hydroxybenzaldehyde

Industrially useful alkylphenyl sulfides are produced in high yield from phenyl mercaptan as a raw material by reaction of the phenyl mercaptan with an alkyl alcohol or dialkyl ether, or alkyl mercaptan or dialkyl sulfide having 1 to 4 carbon atoms as a novel alkylating agent at an elevated temperature, for example, 150.degree. to 600.degree. C, in a gaseous phase.

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Akashi, Japan

Masao Kawamura